


How I Met My Boyfriend

by orphan_account



Category: Supernatural
Genre: Alternate Universe - High School, Bisexual Dean Winchester, Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester Mutual Pining, F/M, First Kiss, Fluff, Jock Dean Winchester, M/M, Minor Jessica Moore/Sam Winchester, Mutual Pining, My First Work in This Fandom, Oh my god just kiss already, Pansexual Castiel (Supernatural), Past Castiel/Hannah (Supernatural), Past Castiel/Meg Masters, Past Lisa Braeden/Dean Winchester, Quiet Castiel (Supernatural), Tooth-Rotting Fluff, Young Love, Young Sam Winchester, auuuughgh so clueless
Language: English
Status: In-Progress
Published: 2020-07-29
Updated: 2020-08-04
Packaged: 2021-03-05 23:49:25
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,880
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25573873
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Castiel Novak is living his quiet life as a sophomore in Lawrence High School. This all changes one day when his best friend, Charlie Bradbury, introduces him to Dean Winchester, a jockish junior. A fic that will have you saying, "oh my god, just kiss already," How I Met My Boyfriend is one very, very fluffy ride.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, Castiel/Hannah (Supernatural), Castiel/Meg Masters, Charlie Bradbury & Castiel, Charlie Bradbury & Castiel & Dean Winchester, Charlie Bradbury & Dean Winchester, Charlie Bradbury/Gilda, Jessica Moore/Sam Winchester, Lisa Braeden/Dean Winchester, Lucifer/Meg Masters
Comments: 6
Kudos: 10





	1. Mornings

**Author's Note:**

> Hi everyone! This is my first work in the world of Supernatural. I like this specific genre of High School Fluff so much, I thought, "huh, why don't you just write your own, dumbass?" Please enjoy, and follow me on Tumblr: @double-triple-quadruple-gay! And fan artists, even though my work probably won't blow up, like at all, feel free to make all the art! <3

"Okay, let's see. Notebooks, homework folder, phone. Everything's there." Castiel adjusts his backpack on his shoulder and puts his earbuds in his ears. Music plays, and a calming sensation rushes over him. Music is a useful tool in Castiel's toolbox, especially when stepping onto the bus. The background roar of high school students hits Cas's ears, but he tunes it out.

Unlucky for poor Cas, none of his (very few) friends live in his neighborhood, so he has to sit alone, or with a random person, every day. Sometimes, he thinks he should make a friend on this bus, but that's hard, and requires social effort, so he never does. The only reason that he only has friends is because of their relatively extroverted tendencies, especially Hannah and Charlie, his best friend.

Charlie was already extroverted, but she became friends with literally everyone after she hacked into the school's system and changed grades, the lunch menu, and the morning news show's script.

On the other hand, Hannah became friends with everyone through more... legal means. She's the 10th-grade representative on the student council, so naturally, she has a lot of connections.

Being friends with those two works out well for Cas, as their "kinda cool but not truly popular" status prevents him from being harassed. However, it's kind of awkward when someone strikes a conversation with one or both of them while he's standing right there, and more than a few times, someone has "shipped" Charlie and Cas, or Cas and Hannah, since he's always hanging around. He never had the heart to tell them that Charlie's a flaming homosexual (with a girlfriend) and that Cas and Hannah did date for a little while, but they decided that they would be better off as friends since the majority of their relationship was watching Wheel of Fortune with the vigor of old ladies.

Today on the bus, Castiel is alone, which he, of course, prefers. Being alone means you can stretch out your feet and put your head on the window, and it means that you don't have to deal with awkward "Can I sit here"s and "That's fine"s and the occasional awkward small talk with the really annoying kids.

Cas is also, somehow, in the back, which means he can observe the chaos. Today, it looks like the brothers Michael and Lucifer are fighting again. They always seem to be at each others' throats.

Michael is the football captain, the it-boy, the stereotype. Many girls would describe him as perfect. One time, he even heard someone describe him as "a work of art with rock-hard muscles and a jawline chiseled by Michelangelo."

Then, there's Lucifer. Another stereotype, he embodies the outcasts, the John Benders of the world, just somehow even less likable. Naturally, he and his twin brother do _not_ get along.

Normally, they ignore each other, but today, they're at each other's throats, which only happens ever so often, and it's always apocalyptic.

Cas feels especially bad for their little brother Gabriel, who is forgotten, and only remembered when a brother wants him to pick a side. Being the forgotten younger brother can take its toll, though, so he acts out.

Castiel almost wants to take his earbuds out to listen, but he decides against it. Music is better than arguments, anyway. Arguments make him uncomfortable, and he'd be thinking about it all day.

Tuning out the world once again, he pulls up the Kindle app on his phone and begins to read. Cas never gets motion sick, and his friends get jealous every time they go to an amusement park. Charlie always ends up throwing up, though that may be due to her deep need to eat something from every food cart they pass by.

Suddenly, the bus comes to a stop, and he files off with everybody else. Since the bus always gets to school early, Castiel and his friends hang out in the library before classes start.

"Cas!" Charlie waves from a table in the back left corner where she, Hannah, and her girlfriend, Gilda, all sit.

"Charlie." he sighs.

Charlie raises her eyebrows. "You don't have to be so happy to see me."

"Sorry. I'm just tired."

"That's because you don't sleep." Hannah looks up from her book.

"I don't need to. Studying is more important," Cas declares.

"Dude. You gotta take care of yourself sometimes!" Charlie's eyes widen. "You don't eat breakfast, pretty much all you eat for lunch is a piece of fruit, and, like Hannah said, you never sleep."

"What's your point?" Castiel sighs, "I'm doing just fine."

"Clearly you're not." Hannah chimes in.

"You know what you need? A little pick me up. You need to go on a date."

"Charlie," Castiel warns.

"Come on! You haven't gone on a date since you broke up with Meg."

Meg was Cas's other girlfriend. They were together for a good three months before he finally dumped her. It was a whirlwind of a relationship, filled with a lot of passion from her end and not as much from his. Sure, he liked her. Meg was very attractive (or, as Charlie would put it, really fucking hot) and a great person (in her own way) but definitely not right for him. It kind of soured the whole "dating" thing for him.

"Yes, well, I regret Meg, and I don't want to enter another situation like that."

"You can't hide from dating forever just because of one bad experience!"

"Watch me." Cas retorts. Charlie pouts in defeat.

"Guys, we're going to have to get to class in a bit," Hannah says.

Charlie checks her phone. "Oh, shit, yeah," she says, picking up her stuff. "Later, bitches."

"Goodbye, Charlie," Cas waves.

-

"Sam, did you eat breakfast?" Dean yells. He hasn't eaten yet and he probably won't, but his brother is more important.

"Yes, Dean, I have eaten breakfast! Worry about yourself!" his brother, Sam, shoots back.

Dean could never worry about himself. His brother was just too important. Their dad was always out on business trips, and their mother was long-dead, so he acts as Sammy's mother, father, and older brother.

"Sam, I'm leaving in a few minutes. You better be out here in 5, or you're taking the bus!"

"Okay, okay!" Sam grumbles. "I'm out, Dean. Let's go."

Dean ruffles Sam's hair. "Okay, buddy."

The two load their stuff into the Impala, Dean's prized car. It used to be his dad's, but he rarely needed his car anymore, since he was always away.

"So," Dean says, to pass the time, "how's the advanced high school classes going?"

Sam, being the super-genius that he is, starts out his day at the high school with advanced math classes. Then, he's bused over to the middle school, and then Dean picks him up on his way home.

"Fine, Dean," Sam mutters.

"Aw, come on, Sammy," Dean whines, playfully. "You can tell me, I'm your older brother!"

"They're okay. I'm doing good, I think."

"Nobody's giving you a hard time, or anything?" Dean says in a stern tone.

"Nah. They all have pretty much adopted me as their little brother."

"Good," Dean says, refocusing on the road.

When the brothers pull up to the school, Sam hops out immediately.

"Library," he says before Dean can ask. "They have a lot better books than the middle school."

"Ah," Dean nods.

After waving goodbye to Sam, he makes his way over to the football field, where the rest of the team waits for him. Michael, the captain, sends a sideways glance his way, but he doesn't pay much attention to it.

Michael. Dean hates Michael. As he so elegantly puts it, Mike has "a whole fucking oak tree up his ass". And his brother, Lucifer, is no better. A lot looser, and way more fun, but a huge dickwad. The only family member that Dean can tolerate is Gabriel. He can be annoying, but he's nice, sometimes.

Dean spends a few minutes on the field with his football buddies, scrolling through Instagram while they talk about upcoming games and the like. Then, they get to talking about Homecoming.

Homecoming. Since it's late August, it's only about a month and a half away. Dean never really liked school dances, but Homecoming is usually very fun for him.

Last Homecoming, he took Lisa Braeden. It was super fun, and they danced and drank the night away. Their relationship did not end on great terms, but Dean was glad that he could dig up some good memories.

While scrolling through his phone, Dean wonders if he'll even go to Homecoming this year. The end with Lisa was so bad that he steers clear of dating altogether. Dean doesn't need to feel hurt like that again.

Not for anyone.


	2. Introductions

**Summary for the Chapter:**

> Castiel and Dean's worlds collide when a good friend introduces them.

**Notes for the Chapter:**

> Hey guys! This is, of course, my first fic, so even just the (as of now, Thursday, July 30th) three kudos and two/three comments really made me super excited to add more! I already have each chapter planned out, I just need to write, lol. 
> 
> As always, love y'all, and check out my Tumblr! @double-triple-quadruple-gay

Another day, another round of boring-ass classes. Castiel sighs as he hugs his books to his chest. Just his luck- none of his friends are in his classes, and he has to go through his day alone until lunchtime.

When he gets to his lunch table, Charlie, Gilda, Hannah, and someone else wait for him. He sits down, confused, until Charlie turns to address him.

"Hey, Cas! Look what I bought!" she says, excitedly.

"Charlie, I don't think you can buy a human." Cas furrows his brows in obvious concern.

Charlie widens her eyes. "Castiel Novak, have you ever seen a goddamn Vine in your godforsaken life?"

"Yes, I have seen a vine, assuming you're referring to a climbing or trailing woody-stemmed plant of the grape family."

"No, Cas, I'm not. And how do you even know the exact definition of the word 'vine'?"

Cas puts his hands up defensively. "I know things, okay? Do not ask me how I know them."

Charlie shakes her head. "Anyway, I brought a friend along to our lunch table."

"I was dragged," the guy shrugs.

"Cas, meet Dean. Dean, meet Cas."

"Hello," Cas mutters.

"Hey," Dean replies.

"Dean is sitting with us today because I wanted him to."

"Honestly, I don't really care. It's nice getting away from the football crowd sometimes. Especially Michael." Dean leans in. "He's very fucking annoying."

A hint of a smile comes across Cas's face before he takes a bite of the single banana he packed in his lunch box.

Dean glances at the banana, then into the box, raising his eyebrows. "Is that _all_ you _eat_?" he says, shocked.

Embarrassed, Cas looks down at his feet. Dean quickly responds with "oh, I'm sorry, I didn't mean it like that! I, uh, eat more than the average human being, so that's like, nothing to me."

"It's no big deal," Cas shifts in his seat. "I know I don't eat much."

"He doesn't sleep much either," Charlie chimes in. "We all think he should take care of himself more."

"Oh, fuckin' same bro. I literally got four hours in the last few days." Dean nods, as if proud of himself. The rest of the group, save Cas, looks shocked.

A flurry of comments from Charlie, Hannah, and Gilda present themselves.

"Oh my God, Dean-"

"That's so bad for your health-"

"Please get some sleep-"

While the girls are ranting about Dean and Cas's terrible sleep schedules, they share a small smile.

"Must be nice to have friends that care so much about you," Dean says.

"I really am," Cas responds. "They found me, and, well, I'm truly grateful. I don't know where I would be without Charlie. Probably sitting alone at that lunch table by the trash."

Dean smiles, vaguely. "Yeah, well, I'm not so lucky. My friends-" he jabs his thumb in the general direction of the so-called "football table"- "don't give a single shit, honestly."

Cas nods. "It be like that sometimes."

"Wait, what?" Dean furrows his brows in confusion.

"Is-Isn't that what you're supposed to say?"

"Um, you're not exactly supposed to? But you could, I guess."

"Dammit. Charlie says that every single time one of us talks about their feelings, so I kind of just figured that’s what you're supposed to say."

"No, no, it's totally fine! It was just kinda weird since you talked all serious and stuff."

"Sooo," Charlie interrupts. The two boys jump a bit, forgetting she was there. "What did I miss?"/p>

Cas opens his mouth to speak, but Dean answers first. "Nothing, really. I was just saying how lucky Cas here is to have friends like you guys."

"Oh," Charlie smirks. "Sounds fun."

Cas sighs. "Charlie-"

"What?"

Castiel is about to complain, but he looks over at Dean, slightly embarrassed. Since he came out as pan, Charlie interprets everything as romantic attraction. However, not many people know, and this being a high school, not many people should know. Life can be hell for young queer kids, and of course, Cas wants to avoid being relentlessly teased. Even Charlie, probably the gayest girl Cas has ever met, hasn't come out to the school quite yet.

Having all of this on his mind, and not knowing how Dean would react, he sighs, glares at her, and says, "Nothing."

Charlie leans back (well, as far back as one can go without falling) and says, "That's what I thought."

As she says that, the bell rings.

"Welp," Charlie says, slamming her hands down on the table, "See y'all tomorrow?" she says, as she looks expectantly at Dean.

"Maybe," he shrugs. "I'll have to see."

As he walks away, Charlie elbows Cas. "What did you think of Dean-o there?"

Cas stares intently at his back. "He was okay, I guess. I might have to get to know him a little bit more."

-

As Dean walks through the halls after lunch, his teammate and close "friend", Uriel, approaches him.

"Hey, dude. Where were you at lunch?"

"Oh, just sitting with Charlie Bradbury and friends." Dean shrugs.

"Oh," Uriel says, as he gives Dean a weird look. "Anyway, Michael has been looking for you."

Dean gives Uriel an equally weird look. "Why?"

He shrugs. "I don't know man, I'm just the messenger."

"Uh, okay. Ummm, is practice still on for today?"

"Yeah, of course," Uriel nods, walking away.

Dean puts in his earbuds and begins to blast classic rock music. Classic rock is his safe place. He knows every word to every Led Zeppelin song. Sam teases him about it and calls him a nerd sometimes, but that doesn't matter. He likes what he likes.

After a dragged-out walk to math class, Dean settles into his seat at the back of the class. Math is not and never will be his "thing." Sammy can have it all to himself.

"How about... Dean?" the teacher says. Not hearing her, Dean continues to stare out the window.

"Mr. Winchester?" Dean still doesn't respond.

His math teacher has to walk all the way over to his desk before he finally raises his head. "Yeah?"

"Can you answer the question?"

"What question?" The class snickers at Dean's expense.

"The one on the board, Dean."

Dean looks at the board and immediately comes up with his answer. "No."

The teacher closes her eyes, all hope for her students dissipating. "Please show up for an afternoon tutorial today, okay?"

Dean doesn't budge. "But I have practice."

"Then tomorrow!"

"Ok, I guess," Dean mutters, bowing his head.

Noticing the time, one student zips up their backpack, which, as is custom of the average American high school, sets off a chain reaction, causing every other student to pack up as well.

"Wait! Guys! I still have to-" the bell rings, cutting off the teacher as the students hastily leave the classroom.

Dean lets out a deep breath and hangs his head. As soon as he begins to walk, he bumps into a familiar redhead.

"Hey Dean!" Charlie smiles, happy as ever.

"Hey Charlie," Dean sighs.

She frowns. "What's wrong?"

"I just had a really, really boring math class."

"Math is boring, yes. But you know what really helps with boredom?"

"What helps with boredom, Charlie?"

"A party!"

Of course. Charlie is always trying to get Dean to have a party because his dad is always gone.

"Really, Charlie? You always want me to have a party."

Charlie pouts. "Yeah, because they're fun."

"I know, but-"

"Please, Dean? Have a party? For me?" she bats her puppy-dog eyes.

Dean rolls his eyes. "Fine. Saturday, okay?"

"Yay!" Charlie cheers and pumps her fist, then cups her hands. "Hey everyone! Dean-o's having a party on Saturday!"

"Charlie!" Dean says. Half the hallway gives Charlie a weird look, and the other half nods in approval.

"What about a party?" A voice interjects, rounding the corner.

"Cas!" Charlie pounces on him.

Castiel does not look amused.

"Yeah," Dean says, scratching the back of his neck. "I, uh, I'm having a party on Saturday. If that's not your scene, I underst-"

"He's coming," Charlie declares.

"I am?" Cas questions.

"Yep. I'll text you his address."

"I guess I have no choice in the matter, so, uh, I will be coming."

"Cool," Dean half-smiles.

"C'mon! Class is gonna start!" Charlie says.

"Since when do you care about class?" Cas says.

"Since I can make you guys walk with me. Come ON!" she grabs Castiel and beckons for Dean.

Dean has no choice but to come.


End file.
